Water → HCID 118199436, compound

HRID 2279986Notes

Reaction equation

HRID 2279986 reaction equation
O1CCCOC1.CC1(C)[O:13][C@H:12](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:11]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:10][O:9]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[OH:9][CH2:10][CH:11]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C@H:12]([OH:13])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 104501,3-DioxaneHCID 118199432HCID 118199432, compound

Product 1

HCID 118199436HCID 118199436, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3-Dioxane, 2-boc amino (10B) and 10 mol % TsOH were combined in 5.0 mL THF and 5.0 mL H2O and stirred at reflux until the starting material was consumed as indicated by TLC. The reaction mixture was quenched with 5% NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, and removed in vacuo. Purification by flash chromatography on silica gel afforded the desired product as a white solid (95%).

Workup

  1. temperatureat reflux until the starting material
  2. customwas consumed
  3. customThe reaction mixture was quenched with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customremoved in vacuo
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-95857a02cdab4f3ca33aba4ddc897266
Source dataset
uspto-grants-2015_09
Patent number
US09133488B2

Reaction notes

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